Polyoxy Patents (Class 568/648)
  • Patent number: 4556746
    Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene; C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxo reaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.
    Type: Grant
    Filed: March 8, 1985
    Date of Patent: December 3, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4556737
    Abstract: This invention provides novel sulfonium compounds, processes for the preparation of the sulfonium compounds, and pharmacological composition containing the sulfonium compound. The compounds of this invention are useful for treating allergy.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: December 3, 1985
    Assignee: Taiho Pharmaceutical Company Limited
    Inventors: Akihide Koda, Mikio Hori, Naosuke Matsuura, Mitsugi Yasumoto, Ichiro Yamawaki, Shuichi Ueda, Yukio Tada
  • Patent number: 4543430
    Abstract: Process for the preparation of addition products of epoxides and hydroxylated compounds, characterized by the fact that it comprises the reaction of an epoxide and a hydroxylated compound in the homogeneous liquid phase, in the presence, as catalyst, of a salt of trifluoromethanesulphonic acid.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: September 24, 1985
    Assignee: BP Chimie Societe Anonyme
    Inventors: Daniel Falgoux, Danielle Simoulin, Michel Pascal-Mousselard
  • Patent number: 4543362
    Abstract: p-Alkyl or cycloalkyl phenoxy alkanols and esters are provided having the structure: ##STR1## in which: R.sub.1 is an alkyl group having from one to six carbon atoms, preferably tertiary, and still more preferably tertiary-butyl; or a bivalent cycloalkylene group condensed with the phenyl group at adjacent ring carbons thereof, such as in indane;R.sub.2 is lower alkyl having from one to three carbon atoms or hydrogen;R.sub.3 is hydroxyl or an ester group selected from the group consisting of COOR.sub.4 and OOCR.sub.4 derived from unsubstituted and hydroxy-substituted monocarboxylic acids and COOR.sub.5 OOC and OOCR.sub.
    Type: Grant
    Filed: January 13, 1984
    Date of Patent: September 24, 1985
    Assignee: Frank M. Berger
    Inventors: Frank M. Berger, Joseph I. DeGraw, Jr., Howard L. Johnson
  • Patent number: 4533759
    Abstract: Ethylene glycol monoaryl ethers useful as fragrance chemicals are obtained by ethoxylating a phenol in the presence of an alkali metal borohydride and alkali metal hydroxide and neutralizing the resulting monoethoxylated product to pH 6.5-7.5 with an aliphatic di- or polycarboxylic acid or hydroxyaliphatic carboxylic acid. Ethylene glycol monophenyl ether having a consistent mild rose odor profile and free of undesirable metallic notes is obtained by the present process.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: August 6, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventor: Eugene G. Harris
  • Patent number: 4521634
    Abstract: Described are ether carbinols defined according to the generic structure: ##STR1## wherein X.sub.1 represents a moiety selected from the group consisting of: ##STR2## and wherein Y.sub.1 represents C.sub.4 or C.sub.5 alkylene or C.sub.4 or C.sub.5 alkenylene or C.sub.4 or C.sub.5 alkynylene; processes for preparing such ether carbinols by means of first reacting allyl ethers with a mixture of carbon monoxide and hydrogen by means of an oxoreaction to produce ether carboxaldehydes and then reducing the thus formed ether carboxaldehydes to ether carbinols; or reacting camphene with appropriate diols; as well as methods for augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes and perfumed articles; foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes; and smoking tobaccos and smoking tobacco articles by adding thereto an aroma or taste augmenting or enhancing quantity of the thus produced ether carbinols.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: June 4, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4518788
    Abstract: Aromatic polyvinylethers and active hydrogen compound reaction products thereof have been found to provide fast heat curable molding compositions when used with various heat activated curing catalysts, for example, diaryliodonium salts in combination with aromatic polyvinylether soluble copper compounds, or dialkylhydroxyarylsulfonium salts in combination with certain organic oxidants.
    Type: Grant
    Filed: January 20, 1983
    Date of Patent: May 21, 1985
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4504685
    Abstract: Hydroxyl compounds are oxyalkylated by contacting them with an alkylene oxide, such as ethylene oxide or propylene oxide, in the presence of a perfluorocarbon polymer containing pendant sulfonic acid groups.
    Type: Grant
    Filed: August 19, 1980
    Date of Patent: March 12, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4497830
    Abstract: Compounds of Formula I ##STR1## wherein X is oxygen or CH.sub.2 ;A is CH.sub.2 --CH.sub.2, trans-CH.dbd.CH or C.tbd.C;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## and the OH groups may be in the .alpha.- or the .beta.-position; D is straight chain or branched, saturated or unsaturated hydrocarbon aliphatic of from 1 to 10 carbon atoms, which may be substituted by fluorine;E is C.tbd.C or CR.sub.3 .dbd.CR.sub.4, R.sub.3 and R.sub.4 being different and being hydrogen or alkyl of 1 to 5 carbon atoms;R.sub.1 is free or functionally modified hydroxy; andR.sub.2 is alkyl, cycloalkyl, optionally substituted aryl or heterocyclic,have valuable pharmacological properties, e.g., hypotensive and bronchodilatory characteristics. They can furthermore be used for prophylaxis and therapy of coronary infarct and as a treatment for stroke. They are produced by means of reduction of the corresponding 1-carbonic acid derivatives.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: February 5, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Gerda Mannesmann, Bob Nieuweboer
  • Patent number: 4495353
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 22, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4493846
    Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or esterified carboxyl group, a hydroxymethyl group, a cyano group, a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7-membered saturated heterocyclic group) or a group of the formula: ##STR3## (R.sup.a and R.sup.b are each as defined above), Y is an ethylene group or a vinylene group, R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sub.1 and R.sub.2, when taken together, means a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: January 15, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Shunsuke Sami, Atsuyuki Kojima, Junki Katsube
  • Patent number: 4453018
    Abstract: An alkylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with an alkyl sulfite of the formula (RO).sub.2 SO in which R is a one to four carbon alkyl group, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4453004
    Abstract: A process for the preparation of an alkylated phenolic ether comprising reacting a phenolic compound at a temperature of at least the melting point of the phenol and in the absence of a solvent with an alkylating agent until an alkylated phenol is produced.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4453017
    Abstract: A methylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with trimethyl phosphate, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4435585
    Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.
    Type: Grant
    Filed: November 17, 1981
    Date of Patent: March 6, 1984
    Assignee: Givaudan Corporation
    Inventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
  • Patent number: 4433179
    Abstract: A process for the preparation of allyl ethers of the formulaR--O--CH.sub.2 --CH.dbd.CH.sub.2).sub.nin which R and n are as defined in claim 1, by reacting hydroxy compounds of the formulaR--OH).sub.nwith allyl chloride or allyl bromide by phase transfer catalysis, 0.8 to 5 mols of allyl chloride or allyl bromide, 1 to 6 mols of aqueous or solid sodium hydroxide and, as the phase transfer catalyst, 2 to 20 mol % of a quaternary ammonium salt, a quaternary ammonium base or a crown ether being employed per hydroxyl equivalent of the compound of the formula II, and the reaction being carried out in the temperature range from 20.degree. to 100.degree. C.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: February 21, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Lohse, Charles E. Monnier
  • Patent number: 4426332
    Abstract: A process for the preparation of resorcinol derivatives of the general formula I ##STR1## where R.sup.1 is carbalkoxy, nitrile, alkyl or H and R.sup.2 to R.sup.5 are H or lower alkyl, by reacting the corresponding cyclohexane-1,3-dione (II) with oxygen or an oxygen-containing gas in the presence of a catalytic amount of a copper compound and of from 1 to 10 moles of a hydrogen halide, or from 0.5 to 5 moles of thionyl chloride per mole of II, in an alkanol having from 1 to 6 carbon atoms, tetrahydrofuran or methyl tert.-butyl ether as the solvent, at from 0.degree. to 150 C., without the addition of a significant amount of water to the reaction mixture. Some of the resorcinol derivatives prepared are useful scents with fragrance notes of the character of the odoriferous substance of natural oak moss.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: January 17, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Thoemel, Werner Hoffmann
  • Patent number: 4424389
    Abstract: A process for producing chroman, a compound of the formula, ##STR1## or an optically active compound thereof wherein R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, which comprises reacting a compound of the formula, ##STR2## or an optically active compound thereof wherein A is an aryl group and R.sub.5 is a C.sub.1 -C.sub.4 alkyl group, with a compound of the formula, ##STR3## wherein R.sub.1 is a C.sub.1 -C.sub.3 alkyl group, X is a halogen atom and R.sub.2, R.sub.3 and R.sub.4 are as defined above, to obtain a compound of the formula, ##STR4## or an optically active compound thereof wherein A, R.sub.1, R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: April 12, 1982
    Date of Patent: January 3, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Yoji Sakito
  • Patent number: 4413149
    Abstract: Disclosed is a process for catalytic hydrogenolysis of p-substituted benzaldehyde-dialkyl-acetals of the general formula ##STR1## in which R is an alkyl group, an unsubstituted or substituted aryl group or an unsubstituted or substituted aralkyl group, by means of a catalyst system composed of cobalt carbonyl and at least one nitrogen-containing heterocyclic compound, such as pyridine, pyrrole, pyrrolidone or piperidine and a hydrogen/carbon monoxide mixture to give the corresponding p-substituted benzyl alkyl ether derivatives.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: November 1, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Fischer, Detlef H. Skaletz
  • Patent number: 4409403
    Abstract: This invention relates to oxyalkylations which take place in the presence of solid acid catalysts. More particularly this invention relates to increasing the selectivity of such processes employing a solid acid catalyst, preferably a polyfluorosulfonic acid catalyst, in which an hydroxylic compound reactant reacts with an alkylene oxide reactant to produce a desired mono-oxyalkylated product which tends to react with the alkylene oxide to produce an undesired second product.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: October 11, 1983
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4404407
    Abstract: Ethylene glycol monoaryl ethers useful as fragrance chemicals and substantially free of undesirable metallic notes are obtained by treating the product with an alkali metal borohydride at a temperature from ambient up to about 100.degree. C.
    Type: Grant
    Filed: June 8, 1981
    Date of Patent: September 13, 1983
    Assignee: Emery Industries, Inc.
    Inventor: Eugene G. Harris
  • Patent number: 4390734
    Abstract: Propylene glycol monoalkyl ethers are prepared in good yield by reacting acetaldehyde and an alkanol (or by reacting an acetal) with carbon monoxide and hydrogen in the presence of a catalyst comprising a cobalt-containing compound and a cocatalyst comprising a member of the group consisting of rhodium-containing compounds, ruthenium-containing compounds and nickel-containing compounds, and heating the resulting mixture at moderate temperatures and pressures for sufficient time to produce the desired glycol monoalkyl ether, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: June 28, 1983
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4390732
    Abstract: Guaiacol glycerine ether is obtained in very good yield and in very high purity by reacting glycidol with o-methyoxyphenol in the presence of an alkali hydroxide, an alkali alcoholate, an alkali cyanate or an alkali thiocyanate at 80.degree. to 150.degree. C. An especially effective purification of the crude product can be obtained by adding hydrogen peroxide, preferably prior to cooling.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: June 28, 1983
    Assignee: Degussa AG
    Inventors: Wolfgang Merk, Rudolf M. Wagner, Peter Werle, Robert S. Nygren
  • Patent number: 4388450
    Abstract: Aromatic polyvinylethers and active hydrogen compound reaction products thereof have been found to provide fast heat curable molding compositions when used with various heat activated curing catalysts, for example, diaryliodonium salts in combination with aromatic polyvinylether soluble copper compounds, or dialkylhydroxyarylsulfonium salts in combination with certain organic oxidants.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: June 14, 1983
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4385190
    Abstract: A process for the production of a mono- or poly-alkylene glycol diether which consists of reacting an ether having at least one lower alkyl group with alkylene oxide in the presence of a heteropoly acid or a heteropoly acid acidic salt. Heteropoly acids and their acidic salts whose ratio of the hetero and coordinate atom is 1:6 and 1:12 are preferably used.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: May 24, 1983
    Assignee: Nisso Petrochemical Industry Company Limited
    Inventors: Yu Ohashi, Norio Sone, Takashi Tobita
  • Patent number: 4380546
    Abstract: Azole compounds of the formula ##STR1## where X is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl or phenyl and m is an integer from 1 to 5, and, if m is greater than 1, the X's can be identical or different, n is an integer from 2 to 5, Z is N or CH and Y is CO or CR.sup.1 OR.sup.2, where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or C.sub.1 -C.sub.4 -alkanoyl, and their crop-tolerated addition salts with acids, and metal complexes.The compounds act as fungicides and growth regulators.
    Type: Grant
    Filed: April 29, 1981
    Date of Patent: April 19, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Eberhard Ammermann, Costin Rentzea, Bernd Zeeh, Johann Jung, Ernst-Heinrich Pommer
  • Patent number: 4368135
    Abstract: Anisotropic compounds with negative or positive DCA and .DELTA.n.ltoreq.0.2 have the formula (1) ##STR1## in which R.sup.1 and R.sup.2 l are independently hydrogen, alkyl, alkoxy having 1 to 12 carbon atoms respectively, or one of R.sup.1 and R.sup.2 can represent cyclical fragment of formulae (1a) or (1b); ##STR2## the bridges Z.sup.1, Z.sup.2 and Z.sup.3 are identical or different and means covalent bonds or carboxyl or oxycarbonyl groups; R.sup.3 is hydrogen, alkyl or alkoxy group having 1 to 12 carbon atoms, respectively; X.sup.1 and X.sup.4 are independently hydrogen, halogen, nitrile or nitro, wherein at least one of X.sup.1 and X.sup.4 is not hydrogen when R.sup.2 represents a cyclical fragment of formula (1a) or (1b) and Z.sup.2 is a carboxyl group or Z.sup.3 is an oxycarbonyl group, respectively. Liquid crystal compositions are also disclosed.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: January 11, 1983
    Assignee: BBC, Brown, Boveri & Company, Ltd.
    Inventor: Maged A. Osman
  • Patent number: 4352760
    Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: October 5, 1982
    Assignee: The Upjohn Company
    Inventor: Kirk M. Maxey
  • Patent number: 4351950
    Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.
    Type: Grant
    Filed: January 2, 1980
    Date of Patent: September 28, 1982
    Assignee: Warner-Lambert Company
    Inventor: Ila Sircar
  • Patent number: 4349487
    Abstract: Phenolic compounds are etherified by contacting at elevated temperature with a mixture of methyl trichloroacetate and either a primary alkyl halide or an aromatic halide containing strongly electron-withdrawing groups in the presence of an initiator.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: September 14, 1982
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4347256
    Abstract: This invention relates to substituted isopentenyl phenyl compounds and their use as anti-juvenile hormones. The compounds have been found effective in the control of insects by inhibiting the actions of juvenile hormones. Such compounds act to induce precocious maturation of immature insects resulting in a reduction in the ecological impact of the insect. Additional effects which have been obtained include sterilization of mature insects. Based on previous research it is also believed these compounds will cause interruption of embryogenesis in insect eggs, the induction of diapause in insects and the prevention of sex pheromone secretion in insects.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: August 31, 1982
    Assignee: Cornell Research Foundation, Inc.
    Inventor: William S. Bowers
  • Patent number: 4341905
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of an alkali metal halide catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: July 27, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4339612
    Abstract: 3,3-Dimethyl-1-phenoxy-butan-2-ols of the formula ##STR1## in which Y is a halogen atom, an optionally substituted phenyl radical, an optionally substituted phenoxy radical or a nitro, cyano, alkyl, alkoxy, alkoxycarbonyl or cycloalkyl radical, and n is 0, 1, 2 or 3,exhibit plant growth stimulating properties and are also useful in the synthesis of known fungicides. They are produced from tert-butyloxirane and the corresponding phenols.
    Type: Grant
    Filed: February 13, 1981
    Date of Patent: July 13, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eckart Kranz, Peter Siegle
  • Patent number: 4333952
    Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen, halogen or C.sub.1-4 alkoxy;X is oxygen; NR.sup.3 in which R.sup.3 is hydrogen, C.sub.1-4 alkyl, or -Y-R.sup.2 ; --C.dbd.O; or --CHOH;Y is --CH.sub.2 --CHOH, and when X is --C.dbd.O it may also be --CH.dbd.CH--; andR.sup.2 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenated;or salts thereof, are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: June 8, 1982
    Assignee: Beecham Group Limited
    Inventor: Brian G. McDonald
  • Patent number: 4314070
    Abstract: An improved process for producing meta-phenoxy benzoic acids and their lower alkyl esters in improved yields and with higher selectivity by reacting an alkali metal phenate with a lower alkyl ester of meta-halobenzoic acid in the presence of a copper sulfate catalyst.
    Type: Grant
    Filed: May 14, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Inc.
    Inventors: Fred G. Schreiber, Peter S. Gradeff
  • Patent number: 4314086
    Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Daniel Michelet
  • Patent number: 4310708
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of phosphonium catalysts.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: January 12, 1982
    Assignee: The Dow Chemical Company
    Inventors: Paul E. Strege, George A. Doorakian
  • Patent number: 4310707
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of Na.sub.2 SnO.sub.3 catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: January 12, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4310706
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of an imidazole catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: January 12, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4307253
    Abstract: Procecss for the preparation of alkyl aryl ethers by reacting phenols with aliphatic ethers in the presence of strongly acid cation exchangers.
    Type: Grant
    Filed: January 7, 1980
    Date of Patent: December 22, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Neumann, Hans-Helmut Schwarz, Dieter Nachtsheim
  • Patent number: 4306097
    Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: December 15, 1981
    Assignee: Pfizer Inc.
    Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4301088
    Abstract: A method for preparing benzyl alcohols or substituted benzyl alcohols is disclosed by decarbonylation of formic acid esters of benzyl alcohols or ring substituted benzyl alcohols, the decarbonylation being carried out in the presence of a catalyst.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: November 17, 1981
    Assignee: Dynamit Nobel AG
    Inventor: Gunther Bernhardt
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4277610
    Abstract: A synthesis of 2,6,10-trimethyl-undecan-1-ol, an intermediate for producing vitamin E, from methacrolein, crotonaldehyde, .beta.-hydroxy-isobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: July 7, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy
  • Patent number: 4273673
    Abstract: There is disclosed a rust inhibitor comprising glycerol-1-alkylphenoxy-3-glycerol ether of the formula ##STR1## wherein R is an alkyl group of C.sub.6-18. A composition having rust preventing effect may be obtained by adding the rust inhibitor to a mineral oil.
    Type: Grant
    Filed: August 23, 1979
    Date of Patent: June 16, 1981
    Assignee: Nippon Oil Company Ltd.
    Inventors: Shoji Kimura, Noboru Ishida
  • Patent number: 4272634
    Abstract: A process for the production of alcohols and/or aldehydes which comprises subjecting a toluene derivative having an ether linkage or linkages of the general formula: ##STR1## wherein RO is an ether grouping where R stands for a hydrocarbyl group with 1.about.20 carbon atoms which may carry an inert substituent or substituents and n stands for an integer of 1.about.2, to auto-oxidation with molecular oxygen in liquid phase to form the corresponding alcohol and/or aldehyde, characterized in that the reaction is carried out by using a lower saturated fatty acid and/or an anhydride thereof as solvent in the presence of a soluble cobalt salt and a bromine ion-supplying substance at a reaction temperature ranging from 30.degree. C. to 200.degree. C. in such manner that the conversion rate of the toluene derivative does not exceed 90%.
    Type: Grant
    Filed: December 11, 1979
    Date of Patent: June 9, 1981
    Assignees: Director-General of Agency of Industrial Science and Technology, Sanko Chemical Co., Ltd., Nippon Soda Co., Ltd.
    Inventor: Juichi Imamura
  • Patent number: 4263449
    Abstract: An alcohol is produced from a compound having an alkenyl group by a hydroformylation of said compound having an alkenyl group in a substantially water immiscible solvent in the presence of a hydroformylation catalyst which is soluble in said solvent and a hydrogenation of the reaction mixture in the presence of a hydrogenation catalyst.Water is added at a ratio of 0.5 to 30 times by weight base on an aldehyde produced by said hydroformylation before said hydrogenation, and an organic phase containing the hydroformylation catalyst component is separated from a water phase containing the alcohol produced by said hydrogenation and said organic phase is recycled into said hydroformylation.The compound having an alkenyl group is an aliphatic olefin, a hydroxyolefin, and olefin ether or an olefin ester and the corresponding saturated alcohol having one more carbon atom is produced.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: April 21, 1981
    Assignee: Toyoda Soda Manufacturing Co., Ltd.
    Inventors: Toshihiro Saito, Yukihiro Tsutsumi, Shoji Arai
  • Patent number: 4261922
    Abstract: Hydroxyalkylphenyl ether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols in the presence of potassium iodide catalyst.
    Type: Grant
    Filed: July 26, 1979
    Date of Patent: April 14, 1981
    Assignee: The Dow Chemical Company
    Inventor: Kenneth M. Kem
  • Patent number: 4254276
    Abstract: Phenolic ethers are prepared starting from phenol or a phenolic derivative and an alkyl carbonate which are reacted at a comparatively low temperature (below 160.degree. C.) and with good yield and selectivity by using a catalytic system composed by a base, preferably a tertiary amine, and by an iodide, either organic or inorganic.
    Type: Grant
    Filed: July 19, 1979
    Date of Patent: March 3, 1981
    Assignee: Anic, S.p.A.
    Inventors: Giuseppe Iori, Ugo Romano
  • Patent number: 4247414
    Abstract: There is disclosed a rust inhibitor comprising glycerol-1-alkylphenoxy-3-ethyleneglycol ether of the formula ##STR1## wherein R is an alkyl group of C.sub.6-18. A composition having rust preventing effect may be obtained by adding the rust inhibitor to a mineral oil.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: January 27, 1981
    Assignee: Nippon Oil Company, Ltd.
    Inventors: Shoji Kimura, Noboru Ishida